EP1904599A2 - Hochleistungsphosphatesterhydraulikflüssigkeit - Google Patents

Hochleistungsphosphatesterhydraulikflüssigkeit

Info

Publication number
EP1904599A2
EP1904599A2 EP06784546A EP06784546A EP1904599A2 EP 1904599 A2 EP1904599 A2 EP 1904599A2 EP 06784546 A EP06784546 A EP 06784546A EP 06784546 A EP06784546 A EP 06784546A EP 1904599 A2 EP1904599 A2 EP 1904599A2
Authority
EP
European Patent Office
Prior art keywords
phosphate
tri
composition
butyl
hydraulic fluid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP06784546A
Other languages
English (en)
French (fr)
Other versions
EP1904599B1 (de
EP1904599A4 (de
Inventor
Terry Calvin Wolfe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solutia Inc
Original Assignee
Solutia Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Solutia Inc filed Critical Solutia Inc
Publication of EP1904599A2 publication Critical patent/EP1904599A2/de
Publication of EP1904599A4 publication Critical patent/EP1904599A4/de
Application granted granted Critical
Publication of EP1904599B1 publication Critical patent/EP1904599B1/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04Mixtures of base-materials and additives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/24Compounds containing phosphorus, arsenic or antimony
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/281Esters of (cyclo)aliphatic monocarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084Acrylate; Methacrylate
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/0405Phosphate esters used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/041Triaryl phosphates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02Unspecified siloxanes; Silicones
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02Pour-point; Viscosity index
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids

Definitions

  • This invention relates to phosphate ester functional fluid compositions and more particularly to such compositions that provide superior performance with respect to flash and fire points as well as extended useful fluid life in service.
  • phosphate esters including trialkyl phosphates, dialkyl aryl phosphate esters, alkyl diaryl phosphate esters and tri aryl phosphate esters.
  • phosphate esters including trialkyl phosphates, dialkyl aryl phosphate esters, alkyl diaryl phosphate esters and tri aryl phosphate esters.
  • Such formulations are disclosed in RE 37,101 to Deetman and are said to provide superior thermal, oxidative and hydrolytic stability.
  • a hydraulic fluid useful in aircraft is available from applicants' assignee under the trademark Skydrol RTM LD4.
  • This composition typically contains 18 to 25% by weight dibutyl phenyl phosphate, 50 to 60% by weight tributyl phosphate, 4 to 8% of butyl diphenyl phosphate, 5 to 10% of viscosity index improvers, 0.13 to 1% of a diphenyldithioethane copper corrosion inhibitor, 0.005% to about 1% by weight, but preferably 0.0075% to 0.075% of a perfluoroalkylsulfonic acid salt antierosion agent, 4% to 8% by weight of an acid scavenger of the type described in U.S. Pat. No. 3,723,320 and about 1% by weight of 2,6-di-tertiary-butyl-p-cresol as an antioxidant.
  • This composition has proved highly satisfactory in high performance aircraft application.
  • compositions containing a mixture of a major amount of tri(n-butyl)phosphate ester and a minor amount of a triaryl phosphate and optionally a minor amount of tri(iso-butyl)phosphate demonstrate improved thermal stability and low temperature viscosity.
  • major amount is an amount at least 50% but not greater than about 80%.
  • the term "minor amount' is an amount less than about 25%, of the total weight of the base stock.
  • many additives are employed in hydraulic fluids, particularly in those fluids employed in aircraft hydraulic systems. Such additives further enhance the properties of the fluid as compared with fluids previously available in the art for use in aircraft hydraulic systems. Typically such additives comprise about 15%, by weight, of the total weight of the fluid. Accordingly, the amount of phosphate ester components provided in the specification and claims is expressed in the percent by weight of the total amount of the final composition, including the additives commonly employed in aircraft hydraulic fluids.
  • the present invention is directed to a fluid composition suitable for use as an aircraft hydraulic fluid.
  • the composition comprises a fire resistant phosphate ester base stock, the base stock comprising between about 50% to about 80%, preferably 55% to about 65% of tri(n-butyl)phosphate, between about 5% to about 15%, preferably between about 8% to about 12% of tri(iso-propylphenyl) phosphate, and up to about 20%, preferably between about 8% to about 12% of tri(iso- butyl)phosphate with the proviso that the sum of proportionate amounts of each base stock component and additives must equal 100%.
  • the high performance fluids of this invention are those that meet the stringent standards of the modern passenger jets. Ih order to meet the needs of the latest high performance jet aircraft fluids employed in the hydraulic systems of such airplanes must have a fluid life of greater than 1000 hours in standard laboratory testing at 0.5% water and 25ppm chlorine content at 125°C, and also a fluid life greater than 10,000 hours at 60°C.
  • the fluid life is defined as the time required for the fluid sample to reach a Neutralization No. of 1.5mg KOH/g sample under the procedure of ASTM D 974.
  • a particularly preferred phosphate ester base stock of this invention is one containing about 60% tri(n-butyl)phosphate, about 10% tri(iso-propylated) aryl phosphate and about 10% tri(n-butyl) phosphate with the proviso that the sum of proportionate amounts of each base stock component together with additives must equal 100%.
  • the phosphate ester base stocks of this invention contain many additives as is well known in the art to provide various beneficial properties to the fluid or aid in preventing degradation or the effects of degradation during use. Such additives are described in RE. 37,101 to Deetman, the entire disclosure of which is incorporated herein by reference.
  • the composition further includes a polymeric viscosity index improver.
  • the viscosity index improver comprises a poly(alkyl methacrylate) ester of the type described in U.S. Pat. No. 3,718,596.
  • the viscosity index improver is of high molecular weight, having a number average molecular weight of between about 30,000 and about
  • the anti-erosion additive is incorporated in an amount effective to inhibit flow- induced electrochemical corrosion, more precisely referred to as zeta corrosion.
  • the anti-erosion additive is preferably an alkali metal salt, more preferably a potassium salt of a perfluoroalkylsulfonic acid.
  • Such anti-erosion additives are more fully described in U.S. Pat. No. 3,679,587 and can include potassium perfluoroethylcyclohexyl sulfonate.
  • additives include corrosion inhibitors such as dihydroimidazole and diphenyldithio ethane, a combination of anti-oxidants such as butylated hydroxyl toluene, 1,3, 5 trimethyl-2,4,6 tris(BHT)benzene and dioctyldiphenyl amine.
  • corrosion inhibitors such as dihydroimidazole and diphenyldithio ethane
  • anti-oxidants such as butylated hydroxyl toluene, 1,3, 5 trimethyl-2,4,6 tris(BHT)benzene and dioctyldiphenyl amine.
  • Still other additives include acid scavengers such as ethylhexyl-epoxycyclohexyl carboxylate and foam inhibitors such as silicone oil.
  • Triaryl phosphates employed in the base stocks of this invention are typically phenyl, but may also be an alkyl-substituted phenyl (alkylphenyl) wherein the alkyl substituent is C 1 to C 9 , preferably C 3 to C 5 .
  • aryl phosphates and alkyl substituted aryl phosphates are, for example, triphenyl phosphate, substituted phenyl phosphates such as tri(isopropylphenyl)phosphate, tri(iso-butylphenyl)phosphate, tri(tert-butyl)phosphate.
  • Triaryl substituted phenyl substituents include tolyl (also known as methylphenyl), ethyl phenyl, isopropylphenyl, isobutylphenyl, tert-butylphenyl, and the like.
  • Preferred triaryl phosphate esters are tri(isopropylphenyl)phosphate and tri(tert- butyl ⁇ henyl)phos ⁇ hate. It is also preferred that the majority of the aryl groups are substituted by only one alkyl group. All percentages expressed in this specification and claims are percent by weight unless otherwise specified.
  • Hydraulic fluids having compositions set forth in Table 1 were prepared by mixing at ambient temperature in a suitable container agitated to provide adequate mixing. The phosphate ester components were introduced into the tank last. The other additives were added first in the sequence indicated in Table 1.
  • IPTPP refers to iso-propyltriphenyl phosphate ester.
  • Van Lube refers to a commercial rust inhibitor, available from Vanderbilt as Van Lub RIG.
  • FC-98 refers to an antierosion agent comprising a potassium salt of perfluoroethylcyclohexy sulfonic acid, also known as perfluoroethylcyclohexylsulfonic acid.
  • IONOL refers to 2,6-di-tert-butyl-p-cresol, an antioxidant, commercially available from Shell Chemical Company.
  • E-330 refers to l,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl hydroxyphenyl)benzene, an antioxidant, commercially available under the trade designation Ethanox.RTM. 330 from Ethyl Corporation.
  • DODPA dioctyl diphenyl amine available from Vanderbilt
  • FH- 132 refers to l,2-di(phenylthio)ethane
  • MCS-1562 refers to 2-ethylhexyl epoxy cyclohexyl carboxylate, available from Dixie Chemicals
  • HF411 refers to poly(butylmethacrylate)
  • HF460 refers to polyalkylmethacrylate polymer in TBP, both are viscosity index improvers
  • Antifoam refers to silicone fluid available from Dow Corning Co. TABLE l
  • Tests were conducted to determine the fire safety, low temperature viscosity, pour point and specific gravity of the fluids described in Table 1.
  • the flash and fire points were determined by means of the procedure of ASTM D-92.
  • the compositions were then tested to determine their properties with regard to autoignition temperature (AIT) under the procedure of ASTM D-2155, viscosity, pour point and specific gravity, hi Table 1, all examples are based upon 100 gram samples. The results of the tests appear below in Table 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)
  • Fluid-Pressure Circuits (AREA)
EP06784546.1A 2005-06-14 2006-06-02 Phosphatesterhydraulikflüssigkeit Active EP1904599B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/152,361 US7582225B2 (en) 2005-06-14 2005-06-14 High performance phosphate ester hydraulic fluid
PCT/US2006/021407 WO2006138081A2 (en) 2005-06-14 2006-06-02 High performance phosphate ester hydraulic fluid

Publications (3)

Publication Number Publication Date
EP1904599A2 true EP1904599A2 (de) 2008-04-02
EP1904599A4 EP1904599A4 (de) 2011-04-13
EP1904599B1 EP1904599B1 (de) 2013-12-25

Family

ID=37523339

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06784546.1A Active EP1904599B1 (de) 2005-06-14 2006-06-02 Phosphatesterhydraulikflüssigkeit

Country Status (14)

Country Link
US (1) US7582225B2 (de)
EP (1) EP1904599B1 (de)
JP (1) JP5058988B2 (de)
KR (1) KR101358716B1 (de)
CN (1) CN101506327B (de)
AU (1) AU2006259750B2 (de)
BR (1) BRPI0612062B8 (de)
CA (1) CA2611874C (de)
ES (1) ES2443241T3 (de)
IL (1) IL188100A (de)
NO (1) NO340217B1 (de)
RU (1) RU2402587C2 (de)
WO (1) WO2006138081A2 (de)
ZA (1) ZA200710844B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2478703C1 (ru) * 2011-12-20 2013-04-10 Российская Федерация, от имени которой выступает Федеральная служба по надзору в сфере защиты прав потребителей и благополучия человека ШТАММ ГИБРИДНЫХ КЛЕТОК ЖИВОТНЫХ Mus musculus 5G6 - ПРОДУЦЕНТ МОНОКЛОНАЛЬНЫХ АНТИТЕЛ, СПЕЦИФИЧНЫХ К V АНТИГЕНУ Yersinia pestis
WO2017099956A1 (en) * 2015-12-07 2017-06-15 Exxonmobil Research And Engineering Company Functional fluid compositions containing erosion inhibitors
US10113131B2 (en) * 2017-01-11 2018-10-30 The Boeing Company Phosphono paraffins
CN113073000A (zh) * 2021-03-08 2021-07-06 安徽中天石化股份有限公司 一种提高磷酸酯抗燃液压油性能的方法
WO2024004763A1 (ja) * 2022-06-27 2024-01-04 三洋化成工業株式会社 粘度指数向上剤組成物及び潤滑油組成物

Citations (2)

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Publication number Priority date Publication date Assignee Title
US3862048A (en) * 1972-05-01 1975-01-21 Mc Donnell Douglas Corp Functional fluid compositions
WO2000024848A1 (en) * 1998-10-23 2000-05-04 Exxonmobil Research And Engineering Company Phosphate ester base stocks and aircraft hydraulic fluids comprising the same

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US3679587A (en) 1970-03-10 1972-07-25 Monsanto Co Functional fluid compositions containing perfluoro surfactants
BE792993A (fr) 1971-12-20 1973-06-19 Monsanto Co Compositions de fluides fonctionnels contenant des stabilisantsepoxyde
JPS5229995B2 (de) * 1972-12-19 1977-08-05
US4324674A (en) * 1980-08-28 1982-04-13 Chevron Research Company Amine salt stabilized phosphate ester-based functional fluid
USRE37101E1 (en) 1992-06-11 2001-03-20 Solutia Inc. Stabilized phosphate ester-based functional fluid compositions
EP0871690A1 (de) * 1994-12-09 1998-10-21 Chevron U.S.A. Inc. Hydraulische flüssigkeiten zur verwendung in flugzeugen
ATE371714T1 (de) 1998-10-23 2007-09-15 Exxonmobil Res & Eng Co Verwendung von phosphatesterhaltigen basisölen als flugzeughydraulikflüssigkeit

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
US3862048A (en) * 1972-05-01 1975-01-21 Mc Donnell Douglas Corp Functional fluid compositions
WO2000024848A1 (en) * 1998-10-23 2000-05-04 Exxonmobil Research And Engineering Company Phosphate ester base stocks and aircraft hydraulic fluids comprising the same

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
See also references of WO2006138081A2 *
Solutia Inc.: "SKYDROL Type IV Fire Resistant Hydraulic Fluids LD-4 / 500B-4", , 2003, XP002621327, Retrieved from the Internet: URL:http://www.nibsoil.com/main-products/SKYDROL%20HYDRAULIC%20OILS/SKYDROL-4-4-25/Skydrol_4_4-25.pdf [retrieved on 2011-02-08] -& Solutia Inc.: "SKYDROL LD4 Material Safety Data Sheet", , 23 August 2001 (2001-08-23), XP002621328, Retrieved from the Internet: URL:http://www.aopis.org/Skydrol%20LD-4.pdf [retrieved on 2011-02-08] *

Also Published As

Publication number Publication date
RU2402587C2 (ru) 2010-10-27
BRPI0612062B1 (pt) 2016-11-08
WO2006138081A2 (en) 2006-12-28
IL188100A (en) 2012-02-29
BRPI0612062A2 (pt) 2010-10-13
KR101358716B1 (ko) 2014-02-07
WO2006138081A3 (en) 2009-04-23
CA2611874C (en) 2014-02-25
US20060278846A1 (en) 2006-12-14
RU2008101389A (ru) 2009-07-20
CA2611874A1 (en) 2006-12-28
NO20080189L (no) 2008-01-11
JP2008546871A (ja) 2008-12-25
EP1904599B1 (de) 2013-12-25
KR20080050386A (ko) 2008-06-05
JP5058988B2 (ja) 2012-10-24
ES2443241T3 (es) 2014-02-18
NO340217B1 (no) 2017-03-20
ZA200710844B (en) 2009-12-30
IL188100A0 (en) 2008-03-20
BRPI0612062B8 (pt) 2017-03-21
AU2006259750A1 (en) 2006-12-28
US7582225B2 (en) 2009-09-01
EP1904599A4 (de) 2011-04-13
AU2006259750B2 (en) 2011-02-10
CN101506327B (zh) 2014-06-04
CN101506327A (zh) 2009-08-12

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